Water → 1-[(E)-3-bromo-1-propenyl]-4-isopropylbenzene

HRID 272346Notes

Reaction equation

HRID 272346 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7](/[CH:10]=[CH:11]/[CH2:12]O)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].P(Br)(Br)[Br:15].O>C(OC(C)C)(C)C>[Br:15][CH2:12]/[CH:11]=[CH:10]/[C:7]1[CH:8]=[CH:9][C:4]([CH:1]([CH3:3])[CH3:2])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24614Phosphorus tribromideHCID 21961314(2E)-3-[4-(Propan-2-yl)phenyl]prop-2-en-1-ol

Product 1

HCID 219613131-[(E)-3-bromo-1-propenyl]-4-isopropylbenzeneYield 107.4%

Reagents, catalysts & solvents 1

HCID 7914Diisopropyl EtherSolvent

Procedure

To a solution of (E)-3-(4-isopropylphenyl)-2-propen-1-ol (10.5 g, 59.6 mmol) in isopropyl ether (100 ml) was added under ice cooling phosphorus tribromide (10.7 g, 39.7 mmol) and the resulting mixture was stirred at room temperature for 30 minutes. Water was added into the reaction solution and the product was extracted with isopropyl ether. The organic layer was washed with water and an aqueous saturated solution of sodium hydrogen carbonate, dried on magnesium sulfate, filtered, and then concentrated under reduced pressure to obtain 10.2 g (72% yield) of the oily title compound.

Workup

  1. extractionthe product was extracted with isopropyl ether
  2. washThe organic layer was washed with water
  3. dry with materialan aqueous saturated solution of sodium hydrogen carbonate, dried on magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3924918bf9924126bf837cc07e489cfc
Source dataset
uspto-grants-2008_11
Patent number
US07456162B2

Reaction notes

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